NP-MRD: Showing NP-Card for 3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid (NP0321592)

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Record Information

Version

2.0

Created at

2022-09-11 23:52:49 UTC

Updated at

2022-09-11 23:52:49 UTC

NP-MRD ID

NP0321592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid

Description

3-[2-Ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-octadecahydrochrysen-1-yl]propanoic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid is found in Plenckia populnea. 3-[2-Ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-octadecahydrochrysen-1-yl]propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171510112D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171510112D          

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    1.1589   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015   -0.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -0.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(C)CCC2C(C)(CCC3(C)C4CC(C)(C)CCC4(CO)CCC23C)C1CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O3/c1-8-26(4)12-11-22-27(5,21(26)9-10-24(32)33)14-15-29(7)23-19-25(2,3)13-17-30(23,20-31)18-16-28(22,29)6/h21-23,31H,8-20H2,1-7H3,(H,32,33)

> <INCHI_KEY>
UEEAECPGUNVURR-UHFFFAOYSA-N

> <FORMULA>
C30H52O3

> <MOLECULAR_WEIGHT>
460.743

> <EXACT_MASS>
460.391645534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
56.46428717406676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-octadecahydrochrysen-1-yl]propanoic acid

> <ALOGPS_LOGP>
6.47

> <JCHEM_LOGP>
7.059793932333335

> <ALOGPS_LOGS>
-6.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.886000683761825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.929126243310691

> <JCHEM_PKA_STRONGEST_BASIC>
-1.099063707923103

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
134.8365

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -0.214  -8.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.190  -6.618   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.184  -4.674   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.171  -3.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.684  -3.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.196  -4.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.708  -4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.757  -3.456   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.253  -4.752   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.220  -8.779   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.212  -9.943   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.684  -7.906   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.659  -3.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.147  -2.959   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.357  -1.503   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.869  -1.212   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.651  -0.339   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   28                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   10   28                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   14   22   24                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    7   12   27                                             
CONECT   27   26                                                            
CONECT   28    8    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3-[2-Ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-octadecahydrochrysen-1-yl]propanoate	Generator

Chemical Formula

C₃₀H₅₂O₃

Average Mass

460.7430 Da

Monoisotopic Mass

460.39165 Da

IUPAC Name

3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-octadecahydrochrysen-1-yl]propanoic acid

Traditional Name

3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CCC1(C)CCC2C(C)(CCC3(C)C4CC(C)(C)CCC4(CO)CCC23C)C1CCC(O)=O

InChI Identifier

InChI=1S/C30H52O3/c1-8-26(4)12-11-22-27(5,21(26)9-10-24(32)33)14-15-29(7)23-19-25(2,3)13-17-30(23,20-31)18-16-28(22,29)6/h21-23,31H,8-20H2,1-7H3,(H,32,33)

InChI Key

UEEAECPGUNVURR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Plenckia populnea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Steroid acid
Steroid
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.47	ALOGPS
logP	7.06	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.84 m³·mol⁻¹	ChemAxon
Polarizability	56.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73880575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid (NP0321592)

MOL for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

3D MOL for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

3D SDF for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

3D-SDF for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

PDB for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

3D PDB for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

SMILES for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

INCHI for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

Structure for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)

3D Structure for NP0321592 (3-[2-ethyl-6a-(hydroxymethyl)-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysen-1-yl]propanoic acid)